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The Ultimate Obama Insider

Jarrett in her office at the White House, where her
influence leaves few fingerprints.Credit
Nadav Kander for The New York Times

On Jan. 25, 2008, the day before the South Carolina Democratic primary, Barack Obama endured a grueling succession of campaign events across the state. When his staff informed him that the evening would conclude with a brief show-up at the Pink Ice Ball, a gala for the African-American sorority Alpha Kappa Alpha, Obama flatly refused to attend. “I’ve been to sorority events before,” he said. “We’re not gonna change anybody’s mind.”

Rick Wade, a senior adviser, Stacey Brayboy, the state campaign manager, and Anton Gunn, the state political director, took turns beseeching their boss. The gala, they told Obama, would be attended by more than 2,000 college-educated African-American women, a constituent group that was originally skeptical of the candidate’s “blackness” and that the campaign worked tirelessly to wrest from Hillary Clinton. State luminaries like Representative James Clyburn — himself an undeclared black voter — would be expecting him. They would be in and out in five minutes.

The three staff members knew what their only option was at this point. “If you want him to do something,” Gunn would later tell me, “there are two people he’s not going to say no to: Valerie Jarrett and Michelle Obama.”

At the day’s penultimate event, a rally in Columbia, Gunn, Brayboy and Wade pleaded their case to Jarrett, the Obamas’ longtime friend and consigliere. When they were finished, Jarrett told them, “We can make that happen,” as Gunn would recall it. Jarrett informed Michelle of the situation, and when the candidate stepped offstage from the rally, Obama’s wife told him he had one last stop to make before they called it a night.

Then Jarrett glided over to the fuming candidate. Her voice was very quiet and very direct.

“Barack,” she said, “you want to win, don’t you?”

Scowling, Obama affirmed that he did.

“Well, then. You need to go to Pink Ice.”

“And he shuts up,” Gunn recalls, “and gets on the bus.”

One year later, Barack Obama convened his first presidential town-hall meeting, in Elkhart, Ind. Responding to a question about the economy, Obama took the opportunity to warn corporate recipients of TARP money that “you are not going to be able to give out these big bonuses until you pay taxpayers back. You can’t get corporate jets. You can’t go take a trip to Las Vegas or go down to the Super Bowl on the taxpayers’ dime.”

Officials in the already-reeling hospitality industry felt sucker-punched by Obama’s remark. “We began experiencing a serious downturn in business,” Jonathan Tisch, the chief executive of Loews hotels, told me. “There were mass cancellations, especially from the financial-services sector.” Tisch commiserated with Penny Pritzker, a developer, hotel entrepreneur and Obama campaign adviser, and word got around to her good friend and fellow Chicago businesswoman, the White House senior adviser Valerie Jarrett.

Jarrett raised their concerns with the president during his morning senior staff meeting. Obama was dismissive. His comments, he said to Jarrett, were not directed at ordinary business travelers but rather at companies that were bailed out at taxpayers’ expense. “And he moved on,” says an administration official familiar with the conversation, who asked not to be named because he was not authorized to speak on the subject. “It was a done deal — the president had spoken. But Valerie has a lot of credibility with him, and she can speak to him honestly. So she decided to go back to the president.”

“This is still an issue,” she told Obama on the morning of March 11, during an economic briefing in the Oval Office. “Even though you said what you said, people are taking it a different way, and it’s hurting the industry.”

The president relented. Obama directed Robert Gibbs, his press secretary, to clarify his remarks. Jarrett didn’t think that was enough, however. Before the meeting broke up, she mentioned that her staff had arranged for a dozen hospitality-industry chief executives to gather in the Roosevelt Room that morning with Obama’s economic adviser Lawrence Summers. Jarrett had just learned that Summers might miss the meeting. Why not seize the moment, she urged Obama: “Let them hear from the president directly.”

A few minutes later, Jarrett left the Oval Office, walked down the hall to the Roosevelt Room and greeted the travel executives. She had barely finished telling them, “The president really cares about this,” when the door flew open, and Obama strolled in. He shook everyone’s hand and then, to their astonished delight, took a seat. For the next half-hour, he listened closely and asked pointed questions. “It was the first time,” one amazed participant would later say, “that any president has sat down with our industry in any meaningful way.”

Before departing, Obama gestured to the unassuming African-American woman at the other end of the conference table. “Valerie’s my business liaison,” he told them. “She’ll be working very closely with your industry.”

That Jarrett had pulled strings to facilitate the meeting was inferred by the C.E.O.’s, one of whom said, “It all happened because one of his senior advisers clearly has a feel for things.” The executive didn’t know that the “feel” ran deeper than policy — that it was about trust: if Valerie Jarrett told Barack Obama that something was the right thing to do, he would very likely do it.

“I mean, he’s really by far smarter than anybody I know,” Valerie Jarrett said one morning this spring in her spacious West Wing office while elaborating on her close friend, the president. Jarrett is divorced and has a daughter, who attends Harvard Law School. She lives in the same Georgetown apartment complex as her close Chicago friends Desirée Rogers, the White House social secretary, and Susan Sher, the first lady’s chief of staff. She tends to dress elegantly, as if planning to head straight from the office to an evening event (which is often the case), and that day was no exception. She also tends to keep her emotional thermostat set at room temperature, much like the president — unless the subject is the president, in which case the 52-year-old Jarrett can be almost breathless, as was the case now. “Not just smart-intelligent,” she went on, “but he’s perceptive, he watches body language. We just had a meeting, and one of his staff people. . . .” Jarrett offered a knowing smile. “If you weren’t really paying close attention, you wouldn’t notice that she was getting rather emotionally involved in the issue. It was clearly — to me, as a woman — something she cared passionately about. And I was watching him look at her, and he’s reading her completely. I look around at the other guys in the room. And none of ’em got it. None of ’em got it!”

“But you got that he got it,” I ventured.

“Oh, yeah,” she acknowledged casually. “Well, I know him pretty well. So I could tell by the look on his face. And I would’ve bet a dollar that when the meeting was over, he was going to hold her back. Sure enough, he said to her, ‘I want to talk to you for a second.’ ”

Among the narrative threads that course almost uninterrupted throughout the history of the American presidency is the inevitable presence in the White House of The One Who Gets the Boss. Karen Hughes got George W. Bush. Bruce Lindsey got Bill Clinton. Jim Baker got the elder Bush. And so on, back to William Seward’s evolving closeness with Abraham Lincoln and Thomas Jefferson’s lifelong reliance on the counsel of James Madison. Each such aide has served his or her president in a way that reveals the latter’s psychology. H. R. Haldeman understood the abiding social discomfort of Richard Nixon (who preferred communicating by memo, at times even with his own wife), and Haldeman spent much of his time as chief of staff keeping others away from the Oval Office. Bert Lance alone among the Georgians in Jimmy Carter’s White House could divine when their fussy boss required a budget-policy huddle, a joke or a moment of prayer. Michael Deaver, the deputy chief of staff who Nancy Reagan would say was “like a son” to Ronald Reagan, deployed the latter’s sunny aloofness with a P.R. man’s acumen, thereby elevating the former “Grade B movie actor” to Great Communicator status.

Valerie Jarrett is a Washington outsider with a Washingtonian’s mind-deadening job title: senior adviser and assistant to the president for intergovernmental affairs and public engagement. Roughly translated, she is Obama’s intermediary to the outside world. But Jarrett is also the president’s closest friend in the White House, and it is not lost on her colleagues that when senior staff meetings in the Oval Office break up, she often stays behind with the boss. Her influence leaves few fingerprints. Over a four-month period of reporting, I struggled to understand Jarrett’s ineffable raison d’etre in the Obama White House. Perhaps proving that nothing succeeds like failure, my plaintive queries were unexpectedly rewarded one afternoon by a telephone call from the president himself. “Well, Valerie is one of my oldest friends,” Obama began. “Over time, I think our relationship evolved to the point where she’s like a sibling to me. . . . I trust her completely.”

Before long, his monologue slid into banality. Jarrett served “as my eyes and ears,” a “sounding board” and was ever helpful with “midcourse corrections.” When Obama was done, I pressed him for clarity. What was unique about their relationship as to make a Valerie Jarrett indispensable to the president of the United States? Surely, I said, it wasn’t simply the longevity of their friendship.

Photo

MIND MELD Jarrett and Obama at
Northern Virginia Community College for
a town-hall meeting on health
care issues. Obama says he runs all
major decisions past her.Credit
Pablo Martinez Monsivais/Associated Press

“No, as I said, she’s someone I trust completely,” Obama replied. “She is family.” Then he hesitated, appraising his own sentiment. “She’s family — she combines the closeness of a family member with the savvy and objectivity of a professional businesswoman and public-policy expert. And that’s a rare combination to have. You know,” he went on to say, “there are other friends of mine who are close to me but who don’t really understand the nature of my work. There are others who are extraordinary experts in policy and politics but don’t have that track record with me.”

Obama then explained what that combination of kinship and competence meant to him. As his surrogate, Jarrett is trusted “to speak for me, particularly when we’re dealing with delicate issues.” At the same time, he could rely on her “to monitor the dynamics inside the White House. She’s got a very good antenna about the disgruntled young staffer or tensions between a couple of principals.” (He declined to be more specific, saying, “Where she serves most ably involves issues that can be sensitive. . . . So I’m not sure I’ve got the killer anecdote.”)

From Obama’s professorial elucidation, those two recurring words — “trust” and “family” — insistently rang out. After our conversation, I began to reflect on Jarrett’s portfolio. Broadly speaking, it consists of “outreach” — endless meetings, conferences and speeches. The kind of job, in other words, that even a president who claims to be all about reaching out might assign to someone he can’t stand. But the bond between Obama and Jarrett indicates that her duties are important to the president, and in a very personal way.

Jarrett functions as Obama’s de facto conduit to the business community. Among the president’s economic team, only Jarrett, the former president of a Chicago real estate development firm, has actually run a multimillion-dollar business. (“The pendulum has swung from an administration that had a lot of experience in business to one that’s filled with regulators and academics,” one of Wall Street’s most prominent chief executives told me recently.) Her street cred with the private sector is an obvious asset to a president confronting a major recession. That said, Valerie Jarrett’s exquisite business connections have been important to Obama since his political ambitions first took hold more than a decade ago. “I think Valerie is the glue between the Obamas and their relationship with the external world,” a mutual friend says. “First Chicago, and then the network expanded exponentially, all over the country. She’s opened a lot of doors.”

Jarrett also serves as the White House’s unofficial champion of minority issues. This may seem superfluous, given that a black man inhabits the Oval Office — until it’s noted that Obama’s inner circle consists largely of white males, same as it ever was. As a top adviser acknowledged, “At the end of the day, when he’s with his closest staff, she’s the only one who has a sense of what it’s like to have a different background from everyone else.”

Jarrett’s shared experience with the Obamas is about race — and on a deeper level, about the coexistence, in the post-King African-American psyche, of conscience and ambition, activism and accommodation. Their identity rests on that fulcrum; it is, as Barack Obama would say, who they are. “I think the thing that’s important to the president and the first lady is this whole notion of authenticity,” says Martin Nesbitt, a Chicago parking-lot entrepreneur whose closeness to Barack Obama rivals that of Jarrett. “And knowing them as well and being as close a friend as she is, Valerie’s always there to say: ‘Yeah, but you know what? That’s not you. You wouldn’t say that. Somebody else is saying that. Barack Obama wouldn’t say that.’ ”

Authenticity has a lot to do with place, of course. Obama was a 23-year-old gifted transient who had yet to connect to the American Experience when he showed up in Chicago in 1985. His quest for identity ended there. “It’s the city that sucked in this kid Barack Obama and made it his home,” Michelle Obama told me. “He considered himself a native of Chicago, because of his community-organizing work, before I ever met him.”

The Obama White House is now populated with as many Chicagoans as it previously housed Texans. Their presence has produced a whipsawing change in ethos at 1600 Pennsylvania Avenue that cannot be explained in strictly partisan, racial or even geographic terms — and of which the new occupants themselves seem unaware. The Texans and the Chicagoans each boast of their larger-than-life politicians, of their native hospitality (be it Southern or Midwestern). “When it comes to family and community, those values are very strong” in Chicago, Michelle Obama told me — eerily echoing the words of Laura Bush at the 2000 Republican National Convention: “Midland was a place of family and community. . . . ”

The similarities end precisely there, because Mrs. Bush finished her thought about Midland with, “and it had a sense of possibility as big as the West Texas sky.” That notion of boundlessness, of pastoral exceptionalism, suffuses the Texas psyche. By contrast, the Chicago that has seen its way through urban malaise, balkanized wards, iron-fisted local governance and epic civil rights clashes has imbued the Obama White House with a far less gauzy mind-set. But the tenets underlying that worldview — struggle is a virtue; united we stand; cities matter — are every bit as fundamental to American idealism as the Texas-bred reverence of vastness and individualism.

The Obamas and Valerie Jarrett experienced firsthand the hard-won progress of a Chicago beset with racial and class divisions during the administrations of Harold Washington, who was the city’s first black mayor, and Richard M. Daley. “There was a certain sense we all shared that people can change, communities can change, cities can change,” Jarrett said when I asked her to talk about what Chicago means to her and the Obamas. “Overcoming adversity not only makes you stronger. It makes you more hopeful. Living through the transformation of the city — maybe we gained our confidence having lived through those days.”

Still, she told me, what Chicago provided Obama with most of all was family — beginning, of course, with Michelle Robinson. “In this narrow question of identity, it was that although they grew up in totally different worlds, she had the same kind of ‘decency and work ethic and sense of responsibility to give something back,’ ” Jarrett said. “But where she was totally different was how she was raised. She had these two parents who loved her dearly and sacrificed greatly so that she and Craig could go to the best colleges. My guess is that her dad was home for dinner every night — he was a huge force in her life — and she had the role model of what a good marriage could be and how to be a role model as a parent. Barack’s mother was very important to him, but he spent a great deal of his life living in a different place. So as all kids do, you always have a fantasy of what perfection would be. And my guess is that Michelle’s childhood was his idea of perfection. It allowed him to anchor himself with her and with her family. To me, that’s the most special thing about Chicago for him.”

It didn’t take long for Jarrett to become part of Obama’s patchwork family. As Daley’s deputy chief of staff, Jarrett was already one of the city’s power brokers in 1991, when her friend and co-worker, Susan Sher, suggested that she take a look at the résumé of a promising young African-American lawyer named Michelle Robinson. The applicant made an impression on Jarrett, and vice versa. “When we interviewed,” Michelle Obama recalls, “we connected because we had similar paths. She’d practiced law but had struggled with some of the same questions: Do I want to stay in a big firm? How do I build a life that’s meaningful and interesting?”

In less than a year, Michelle’s fiancé began to confide in Valerie Jarrett. He showed her pages from a book he was writing. That book, “Dreams From My Father,” explored Barack Obama’s inner struggle in a way that would later astound the friends of his youth, who knew only the mentholated unflappability that prefigured today’s Obama Cool. With Jarrett, he found himself doing what Barack Obama simply did not do: itemizing his self-doubt out loud. “He talked about how hard it was — things he hadn’t dealt with yet,” she recalled. “ ‘It isn’t just a matter of writing a simple story,’ I told him. ‘You’ve got to deal with the fact that your father left you at a very young age. And you lived in a variety of different settings at an age where it could’ve been discombobulating. Your grandparents are white, and you look black. Your friends in Hawaii all are different-looking, and that’s great — but you come to the mainland, and things are much more black and white, literally.’ ”

Jarrett was born of African-American parents in Shiraz, Iran, where her physician father was running a hospital as part of an American aid program. Obama’s fabled “exoticism” was therefore comprehensible to her, the president told me. “I think we both share an appreciation of the world outside our borders that ironically probably makes us appreciate more the values of America,” he said. “It also allows us to maybe travel between worlds and cultures in ways that have proven to be not only professionally important but emotionally satisfying. I guess another way of putting it is, she and I both are constantly looking for links and bridges between cultures and peoples. That’s central to who we are. And that probably has contributed to forging an even closer relationship than we might’ve otherwise had.”

Obama, as his memoir would reveal, sought connection to the heroes of the civil rights movement. Jarrett’s struggle had been of a different sort: how to measure up to the role models who filled her life. Her father, Dr. James Bowman, was an eminent pathologist given to wearing bow ties and trekking his young daughter across Africa for her summer vacations. Equally influential was her mother, Barbara, a childhood-development expert and the daughter of Robert Taylor, the first African-American to head the Chicago Housing Authority.

The fast track laid out for Valerie Bowman — a Massachusetts boarding school, then Stanford, then a law degree at Michigan, then marriage and work at a corporate law firm — was one she pursued without either resistance or zeal, “kind of like an automaton,” she told me. While Jarrett’s family rejoiced when Harold Washington was elected mayor on April 22, 1983, the atmosphere at her nearly all-white firm the next day was one she would remember as “polite silence.” Four years later, as a 25-year-old community organizer was wading into the tumult of her hometown, Jarrett, then 30, decided at last to reconnect herself to it. She quit both her marriage and her job, and in 1987, as the mother of a 2-year-old daughter, she went to work for Mayor Washington’s corporation counsel — relinquishing her high-rise office for a cubicle in the city law department. But like the “sibling” she had yet to meet, Valerie Jarrett had found a path of her own.

Over the next 15 years, her upward trajectory would outpace even Obama’s. Jarrett’s unhappy years as a real estate lawyer now paid off in a city law department tasked with maintaining Chicago’s business base. Washington died of a heart attack in 1987, but her work ethic and supple intelligence distinguished Jarrett in the eyes of Richard M. Daley, who took office two years later. The new mayor promoted her to deputy chief of staff — and later to the post of planning commissioner, thereby baptizing Jarrett in the racially charged torrent of urban affairs.

The experience of infuriating developers and neighborhood groups alike “toughened me greatly,” Jarrett says. From 1991 until 1995, she presided over a rancorous but largely successful makeover of the city’s landscape, tearing down blighted housing projects and relocating residents — those who qualified anyway — to far more attractive new developments in racially mixed neighborhoods. (After her tenure, the infamous projects bearing her grandfather’s name were demolished.) Meanwhile, she was raising her daughter and developing a social life that revolved around an intimate community of like-minded black urban professionals who, like Jarrett, sought advancement not only for themselves but for the local African-American community. Chief among them were the Obamas. Jarrett brought Michelle into the Daley administration, attended their wedding, threw a book-signing party for the “Dreams From My Father” author and generally assumed a big-sisterly presence in the young couple’s lives such that “I don’t think either of them made major decisions without talking to her,” Susan Sher said.

As Obama told me, “We’ve seen each other through ups and downs.” And for Jarrett, one such low point came in 1995, when she began to lose the mayor’s support. Wounded, Jarrett bolted for the real estate development firm Habitat — only to have Daley ask her to keep a foot in the public sector by offering her the post of chairwoman at the Chicago Transit Board. She accepted. Soon other boards beckoned, including the University of Chicago Medical Center and the Chicago Stock Exchange. Habitat made her an executive vice president. By 2002, it was as if the city had awakened one morning to find that Valerie Jarrett had taken over. For Barack Obama, her arrival was right on schedule.

“It was a lousy idea,” Jarrett said as she recalled the decision by Obama, then a state senator, to run for U.S. Senate after he was trounced two years earlier in a bid for Congress. “He called and said: ‘I want to come over. Let’s invite my closest friends. There’s something I want to bounce off of you.’

Photo

THE SIBLING Jarrett and
Michelle Obama in South Carolina
in January 2008.Credit
Jim Wilson/The New York Times

“Well, Michelle had already told me what it was. She said, ‘So we’re not in favor of this, right?’ ‘Absolutely not!’ ‘That’s the right answer!’ We conspired against it for all the obvious reasons. He’d just lost to Bobby Rush. He’d have to raise a ton of cash, and he didn’t have it. The field was unknown. He would have to travel all over the state. Michelle hadn’t been happy about him going off to Springfield, so the thought of him being away more with these two young children was not terribly appealing to her. And she didn’t really think he could win.

“So I cooked breakfast for him, Marty [Nesbitt], John [Rogers, an investment banker and close friend], Michelle and me. And rather than do what he normally does, which is going around the room and say, ‘What do you think?’ he said: ‘I want to run for U.S. Senate. Let me tell you why. I’ve talked to [the veteran state senator] Emil Jones, he’s a huge political force and he’s prepared to support me. When I ran for Congress I didn’t have that kind of support. And if I lose, then Michelle, I’ll give up politics.’ (She’s like, ‘Yes!’) ‘If I can’t do it this time, I promise I’ll get a normal job in the private sector, so this’ll be the last time I ask you to do this — unless I win. And money’s a problem, so Valerie I think you should help me because you’re in the business community, you and John. You two should think about helping me do this.’

“And he did this obviously far more eloquently and for 10 minutes or so. So I said, ‘So, what if you lose?’ He said: ‘If I’m not worried about losing, why are you? If I lose, I lose. But I think I’ll win.’ He didn’t convince me he’d win at that moment. He convinced me that it was worth a try — and that therefore he could. Which is always where he’s kind of been able to get me.”

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Over the ensuing five years, the role Jarrett played in Obama’s political ascent was important but also confined. For his senatorial campaign, she made key introductions to the donor community, which helped the underfinanced candidate achieve legitimacy among a field of well-financed competitors. (At the same time, Jarrett did not dissuade Obama from involvement with the developer and influence peddler Tony Rezko, whom she regarded as “a snake,” according to a friend.) She was among the handful of close advisers who met in the Chicago office of the political strategist David Axelrod at the close of 2006 to carry on a rolling discussion of the risks entailed in a presidential run. And during the first six months of Obama’s presidential campaign, Jarrett remained in constant contact with him but otherwise stayed in Chicago to run Habitat — she had become chief executive in January — and the Chicago Stock Exchange.

That arrangement began to change on the evening of July 17, 2007, when Obama again convened a meeting at Jarrett’s Chicago town house. The presidential campaign was not gaining traction in the national polls, and several of Obama’s associates openly fretted that the emphasis on winning Iowa and the other early states had come at the expense of building a broad base of support across the map. The candidate was also not happy about fielding so many calls from African-American leaders who were critical of the campaign’s “postracial” demeanor. “Lots of things were bubbling up, and no one was really handling issues that would arise, either in Chicago [at headquarters] or on the road,” says Penny Pritzker, who was one of the meeting’s participants and the campaign’s finance chairwoman. “You needed another smart, capable, really close adviser involved who could play a bridging role. Valerie was the perfect solution.”

Not everyone would agree with Pritzker. Though the Obama campaign possessed scarcely a fraction of the melodrama afflicting John McCain’s operation, tension when it did exist tended to revolve around Jarrett. She never actually moved into headquarters, “and that was good and that was bad,” says the White House senior adviser, Pete Rouse, who at that time was Senator Obama’s chief of staff. “In the campaign, that she was sort of outside and free-floating complicated things at times.” Jarrett’s ambiguous role particularly annoyed the campaign manager, David Plouffe, who, several campaign sources say, did not care for her. Jarrett and Plouffe tangled over issues ranging from where the campaign should be spending its money to where the candidate should be spending his time. Outside advisers who could not persuade Plouffe on a matter knew they could then turn to Jarrett as a “court of appeals,” according to a campaign official.

Today Plouffe offers unqualified praise for Jarrett’s work as a campaign surrogate but says, “She wasn’t terribly involved in strategic issues.” This is probably true — but only because the campaign did not consider the matter of race to be a “strategic issue.” On this subject, Jarrett consistently and forcibly weighed in. It was Jarrett, several aides say, who helped convince otherwise skeptical senior staff members that Michelle Obama should go to South Carolina in November 2007 and give a speech addressing fears in the African-American community that harm might come to the black candidate. It was Jarrett who strongly encouraged Barack Obama to give his race speech — convinced when other senior advisers were not, says Dr. Eric Whitaker, a close friend of Obama, “that he could actually pull off the speech,” and that in the wake of the incendiary Jeremiah Wright tapes, now was the time to do it. Numerous campaign officials credit Jarrett, along with the communications director Anita Dunn and Stephanie Cutter, Michelle Obama’s chief of staff, for helping to rehabilitate Mrs. Obama’s angry-black-woman image. (Three staff members say Jarrett encouraged the future first lady to focus on military families.) According to Clifford Franklin, one of the campaign’s African-American media consultants, “Having Valerie at the table kept African-Americans and Hispanics and women at the forefront of our outreach — where before it had been an afterthought.”

As Obama told me, the opportunities afforded him and Jarrett by their predecessors in the civil rights movement gave them both “a shared sense of obligation.” To her and the Obamas, failing to acknowledge the racial dimension of the 2008 campaign constituted dereliction of duty, even if silence on the subject was considered politically expedient by other senior campaign staff members. A moment of truth occurred last July, when the candidate predicted to a Missouri crowd that his opponents would be focusing on how Obama “doesn’t look like all those other presidents on the dollar bills.” Rick Davis, McCain’s campaign manager fired back that Obama had “played the race card, and he played it from the bottom of the deck.” Momentarily flummoxed, the Obama campaign responded with a tepid insistence by Gibbs that the senator was merely “describing that he was new to the political scene.”

“But within the campaign, Valerie had been saying, ‘You guys, you’re not getting this issue right,’ ” recalls a top official. “And Obama communicated to his senior advisers that he thought we were a little gun-shy on race issues; that the reality was, he did look different. There were also African-Americans on our staff, some in relatively senior positions, who were clearly upset that we had not consulted them in the response. And she actually organized a meeting to discuss it.

“And that’s not just a process thing,” the adviser said. “Because moving forward, the candidate made it very clear to us that we were just a bunch of white people who didn’t get it — which, by the way, was true.”

That Obama required the presence of someone who did “get it” inevitably meant that he would want Jarrett in the White House. (“Of course!” Jarrett remembers Obama’s wife exclaiming back in September 2007. “Hasn’t he said anything to you yet?”) Last July, however, Senator Dick Durbin of Illinois floated an intriguing alternative — namely, that Jarrett consider filling the Senate seat that would be vacated by Obama should he win the presidency. The notion gained enthusiastic support from different quarters. To her friends and family, becoming a U.S. senator would allow her to flourish on her own. To less admiring colleagues in the Obama campaign, it meant that they would not have to deal with her in the White House.

Jarrett discussed her options with the Obamas the weekend before the election. The candidate was typically analytical. Michelle was not. Jarrett says: “She came down very hard, saying that’s not what she wanted me to do. She said, ‘We need you in the White House.’ You have to understand. This is right before the election. We’re all really nervous. We knew by that point that chances are he’s gonna win. She’s about to embark on this entirely new episode in her life. And her attitude was like: ‘You’ve come all this way, and you thought this was a good idea, and now you’re gonna bail on me? No way!’ ”

A few days after the election, the president-elect told his new chief of staff, Rahm Emanuel, “I want her inside the White House.” Those who knew Obama understood what motivated his decision. How the decision would play out was less predictable. As one close adviser would say: “It’s like bringing in a family member. You can say all you want that they’ll be held accountable and that you’ll treat them like anybody else. But you can’t.”

One day this past December, Jarrett and her new chief of staff, Michael Strautmanis (formerly a paralegal at the firm where Michelle Obama worked), met in the West Wing with the Bush administration political strategist Barry Jackson. Two of the offices under Jackson’s purview — public liaison and intergovernmental affairs — were about to become Jarrett’s responsibility. After a cordial discussion about the duties she would inherit, Jarrett thanked Jackson and left the building. Strautmanis stayed to finish the meeting. Except for the Roosevelt Room, he had never seen the West Wing before and wondered if Jackson would mind showing him around. Jackson was happy to do so, and they spent a few moments walking the halls. Within a couple of days, Rahm Emanuel himself visited the West Wing to confer with his counterpart, the Bush chief of staff Joshua Bolten. In the course of their conversation, Bolten told Emanuel that Jarrett had been by, looking at office space.

Emanuel was not happy to learn this. He confronted Jarrett, and today he says: “There was a misunderstanding. . . . It wasn’t a dust-up.” As it would develop, Pete Rouse and Jim Messina, the deputy chief of staff, assigned Jarrett the airy second-floor office suite formerly commandeered by Karl Rove and before that the first lady, Hillary Clinton. But Emanuel’s reaction, at bottom, had little to do with West Wing real estate. Instead, it conveyed the understandable wariness with which the other top Obama advisers greeted the only one among them who could claim to be a close personal friend of both the president and the first lady.

When I asked Emanuel what advice he gave Obama on Jarrett’s role in the White House, he smirked and replied, “My two cents to the president stays my two cents to the president.”

“Can you give me one cent?” I asked.

“One cent,” Emanuel said, “was: ‘If you do it, this will be unique, so here are the upsides and downsides we’ve got to be conscious of. This will be different.’ He said, ‘That’s fine, but this is how I would like to do it.’ ”

According to Jarrett, Obama urged her to take on a concretely defined profile, saying, “You don’t just want to come in as my friend, because you could be marginalized.” Rouse suggested the same solution but voiced the opposite concern. He recalls telling her, “If you don’t have line responsibility, you tend to wander, swim outside your own lane and get into other people’s work and irritate people and complicate things.”

Jarrett herself could recognize the potential complications, according to her chief of staff. “She said that one thing she doesn’t want is for people to believe that she would use her relationship with the president and leverage it against them,” Strautmanis told me. “It would be natural for people to have their radar up for that. And I think she’s been successful at establishing to the rest of the senior staff that they can trust her — that she’s not going to back-channel them to the president, that she doesn’t want to be a mini-chief of staff.”

“This town loves and is dying for a whiff of a Rahm/Valerie power struggle,” Cecilia Muñoz, Jarrett’s director of intergovernmental affairs, says. “And there isn’t one.” Certainly that is the case when compared with the gladiatorial clashes within previous administrations. But things have not been seamless between the two — and Muñoz would know, since Emanuel had lobbied her to take the intergovernmental-affairs job without even discussing the matter with Muñoz’s actual boss to be, Jarrett, who at that point had never spoken with Muñoz. The chief of staff has since been respectful of Jarrett’s turf, and the two get along “better than anyone’s expectations,” as Martin Nesbitt delicately puts it. Still, Emanuel talks to a lot of people around town, and when the subject is Valerie Jarrett, it’s fair to say that his words fall short of effusive. Their opposing qualities — deliberateness and sensitivity in Jarrett; speed and brutal practicality in Emanuel — may reside harmonically in Barack Obama. But what the two aides represent isn’t simply a function of velocity or decibel level. While both of them obviously want the president to succeed, Emanuel’s criteria for “success” are straightforward. Jarrett, according to Muñoz, is “very focused on why he ran in the first place” — a psychological calculation that only Jarrett would presume to undertake and which therefore is bound to drive others nuts.

Photo

INSIDE GAME David Axelrod, Valerie
Jarrett, Robert Gibbs, Rahm Emanuel and
a Secret Service agent at a presidential
news conference in June.Credit
Alex Wong/Getty Images

“We have kind of a mind meld,” Jarrett told me about Obama. “And chances are, what he wants to do is what I’d want to do.” Jarrett’s discernment of What Barack Wants has sometimes found her taking unorthodox positions. In recent weeks, senior staff members have fought among themselves over an executive memorandum relating to the Recovery Act. Section 3 of this memo severely restricts contact with White House officials by registered lobbyists to discuss specific stimulus projects. Jarrett has argued that this requirement, while virtuous in theory, means that certain disadvantaged communities — represented, for example, by civil rights organizations whose directors happen to be registered lobbyists — will not be heard. “So there are these tough meetings,” one participant says, “where there are some very strong, very male voices basically saying, ‘The president said we were going to do it this way, and we have to do it this way, come hell or high water.’ And Valerie is one of a group of folks who are saying: ‘You know what? We said we were going to try it. We said we were going to see how it’s going to go. And we need to make sure we do this in a way that’s ultimately consistent with the values we brought to Washington and making sure that we accomplish what we set out to accomplish.’ ”

When I asked Obama if he runs every decision past her, he answered without hesitation: “Yep. Absolutely.” Some of their Oval Office one-on-ones find Jarrett — whose acute familiarity with the business community is unique in the West Wing — playing the impersonal role of trusted financial counselor, the president told me. “Throughout, for example, the debates taking place on how to deal with the financial crisis, I would sit down and get her read in terms of how we strike the appropriate balance between intervention to stem panic and not being so heavy-handed that we were changing in fundamental ways the nature of our free-market economy,” he said. “And her experience as a businesswoman and contacts with C.E.O.’s around the country was very helpful.”

But many of their conversations are far less clinical. Obama as president unburdens himself to his sibling/adviser just as he did while anguishing his way through the writing of “Dreams From My Father.” Jarrett shares his scorn for Beltway insularity and, attuned as she is to his determination not to lose touch with everyday American life, she usually accompanies him to town-hall events. Recalling a flight back on Air Force One with Obama after one such gathering, Jarrett told me: “He talked about — there was one family, nine people in the family lost their jobs. We talked about, ‘What does that do? You can’t even rely on your relatives, no support network.’ We always go through the day’s stories and talk about what touched either of us.”

It’s hard to imagine Obama conducting that kind of empathy session with Emanuel, Gibbs or even Axelrod. “She and Axelrod are the two he’s closest to but in very different ways,” a friend of both advisers said. “He gets brilliant political advice from David, and from Valerie he gets wisdom.” When I asked Axelrod himself to explain how Jarrett’s counsel might prove uniquely valuable to the president, he squinted a little and said: “Well, first of all I think, I mean, he is more likely to come to her with issues of personal concern — family issues, because he has a full plate and she’s also a very close friend. It’s important to have people like that around.”

“Can you recall a particular moment when she’s been that person for him?” I prodded.

The strategist assumed his basset-hound countenance. “There are issues all the time, but, uh, I’m trying to think of some that I would share with you. Because you know the nature of this is that there aren’t that many I want to share because of. . . . I need to think about it.”

Evidently Axelrod does not see in her the utility that Obama does. A weekly Wednesday-night gathering at Axelrod’s house — to discuss what one participant describes as “hard-core politics” — pointedly excludes Jarrett. Otherwise, she attends pretty much whatever she wishes. Though her portfolio — overseeing the Office of Public Engagement (formerly Public Liasion), the Office of Intergovernmental Affairs and the newly created Office of Urban Affairs — is dauntingly packed, her chief of staff, Michael Strautmanis, told me that he sees his job as “to run her office so that she can play that advisory role with the president.” Jarrett therefore has wide latitude over how she spends her day. She assisted her friend Desirée Rogers in selecting a chef for the White House’s Cinco de Mayo reception. Practically on a whim, she spent a day with Michelle Obama in Manhattan and that night donned a black gown to accompany the first lady to Time magazine’s 100 Most Influential People gala.

That Jarrett can pick and choose among meetings and priorities does not exactly ingratiate her with her White House colleagues. On one hand, she has devoted enormous energy to helping Chicago’s campaign for the 2016 Olympic Games — even pledging, rather ostentatiously, to personally direct a department out of the White House that would assist the Games’ operations in her hometown. By contrast, Jarrett has shown little interest in the White House effort to bring the World Cup soccer tournament to the United States in 2018 or 2022. More bothersome to her colleagues was that she seldom attended the senior staff briefings leading up to the Supreme Court nomination of Sonia Sotomayor, even though it was long understood that Jarrett would be on the front lines when the rollout of Sotomayor proceeded.

Still, the Obamas clearly benefit from Jarrett’s ability to freelance. In the early months of the administration, she often stepped in to assist the understaffed Treasury secretary, Timothy Geithner, by communicating with jittery chief executives in the financial-services sector. When Michelle Obama decided last month to beef up her first-lady portfolio, Jarrett slid over to the East Wing to lend a hand. She organized a dinner of the presidential historians Robert Caro, Doris Kearns Goodwin, Michael Beschloss, Douglas Brinkley, Robert Dallek and Garry Wills with her and the Obamas at the White House residence on June 29. And two days later, Jarrett was at the president’s side to moderate a health care town-hall meeting in Annandale, Va.

When I asked Michelle Obama’s chief of staff, Susan Sher, if she had seen Jarrett’s advisory role evolve in ways not anticipated, she smiled abashedly. What she didn’t appreciate then but did now, Sher said, was “how incredibly instrumental she’ll be in virtually everything.”

“Where’s my picture?’’ Valerie Jarrett exclaimed, addressing no one in particular. She stood up from the conference-room table in her office and walked over to the bookshelf. “They brought these to me today.”

She handed me two unframed prints. The first was of Jarrett standing on a staircase with a familiar-looking yellow creature. “I spent five years of my daughter’s life watching ‘Sesame Street,’ ” she said fondly — and indeed, in the photograph with Big Bird, Jarrett wore a meek smile as if in the presence of childhood royalty.

The image I turned to next was no less odd. It featured five figures seated on the couches and chairs of the Oval Office: the president, Jarrett, the Rev. Al Sharpton, the former Republican House speaker Newt Gingrich and the New York mayor Michael Bloomberg. Standing over me, and in a voice no less sentimental than before, Jarrett said, “I love that photo.”

That unlikely meeting — which took place two days after her and Michelle Obama’s appearance on the set of “Sesame Street” — had been arranged by Jarrett. Sharpton, Gingrich and Bloomberg were part of a group convening in Washington to commemorate the 55th anniversary of the landmark Brown v. Board of Education school-desegregation decision by promulgating education as a civil right (though with obvious disagreements among them as to just how this civil right would be advanced). Sharpton had contacted Jarrett to see if a few of them could meet privately with the president so as to obtain the strong backing of Arne Duncan, the secretary of education. At a White House senior staff meeting in the Oval Office, Jarrett brought up the idea of having Sharpton and a few others over to the Oval Office.

“I liked the idea of getting this odd quartet together to come around an issue,” Jarrett told me. “Because it would show the American people that this is what the president is about, getting unlikely combinations together.”

When I talked earlier to Robert Gibbs about the gathering, he mentioned something that I now relayed to Jarrett: “If you would’ve started out a line by saying, ‘Reverend Sharpton, Newt Gingrich and Mayor Bloomberg walked into the White House together,’ I would’ve thought it was the start of a joke.” But the press secretary had also said, “I think it shows how important she thought that event was that it ultimately got on [Obama’s] schedule.” Of course, Gibbs wasn’t exactly saying that he thought such a meeting was important — which, judging by the measured smile on her face, Jarrett seemed to understand.

Pressing the point anyway, I asked, “If you hadn’t suggested that this meeting take place, do you think anyone else would have suggested it?”

Jarrett looked across the table at her friend, the White House communications director, Anita Dunn, who had dropped in on the interview. Dunn stopped taking notes and flashed Jarrett a look of abiding doubt.

“Probably not?” exclaimed Dunn, who had been virtually silent until now. “Absolutely not!”

Dunn’s outburst was freighted with a depth of appreciation that I had not picked up on elsewhere in the West Wing. Though Dunn is white, her words reminded me of the interviews I conducted with several African-Americans who had served at high levels in the Obama campaign. To them, Valerie Jarrett was something of a heroine. As they saw it, she got that Obama’s work as a community organizer in poor black neighborhoods wasn’t just a touching bit of back story but instead bespoke a personal commitment to change. She got the importance of campaigning for better schools and job opportunities for African-Americans, even if such talk wouldn’t make red states turn blue. She got that simply electing a black man would not make all urban traumas disappear. And she got that Obama got it, that this was central to his “authenticity” of which she was guardian — reminding the candidate, “Barack Obama wouldn’t say that.”

Without Jarrett, these officials said they believed, their opinions and the often-legitimate concerns voiced by black leaders like Sharpton would have been thoroughly disregarded by the white-dominated senior staff. “There’s a cultural nuance that they just didn’t get,” one such African-American staff member told me. “And the landscape of our campaign is littered with hundreds of stories where she intervened and voices got heard and decisions got made that might’ve gone a different way.”

As to just how much difference Valerie Jarrett’s various interventions had made, the staff member admitted he couldn’t say. It wasn’t for him to judge, anyway. That was between Obama and Jarrett.

A version of this article appears in print on , on Page MM30 of the Sunday Magazine with the headline: Obama's BFF. Today's Paper|Subscribe